Photopolymerizable aryl and heterocyclic glyoxylamide compositions

Abstract

A photopolymerizable composition comprising photopolymerizable ethylenically unsaturated compounds and, as the photoinitiator, a glyoxylamide having the formula: <IMAGE> I or <IMAGE> II wherein R and R1 are individually selected hydrogen or hydrocarbon of from 1 to 10 carbon atoms; R2 is a heterocyclic radical, aryl of from 6 to 14 carbon atoms or mono-, di- or polysubstituted phenyl with substituents selected from the group consisting of alkyl, alkoxy, aryloxy, alkylthio, arylthio and halogen; R3 is phenyl or-CH2)z WHERE Z IS AN INTEGER FROM 2 TO 6; X is zero, oxygen, sulfur, -NH-, phosphorus or silicon; and n is an integer from 2 to 4. The composition cures upon exposure to actinic radiation.

What is claimed is: 
     
       1. A photopolymerizable composition comprising an ethylenically unsaturated compound and a photoinitiating amount of a glyoxylamide of the formula: ##STR6## wherein R and R 1  are individually selected hydrogen or hydrocarbon of from 1 to 10 carbon atoms; R 2  is a heterocyclic radical, aryl of from 6 to 14 carbon atoms or mono-, di- or polysubstituted phenyl with substituents selected from the group consisting of alkyl, alkoxy, aryloxy, alkylthio, arylthio and halogen; R 3  is phenyl or --CH 2 ) z  where z is an integer from 2 to 6; X is zero, oxygen, sulfur, --NH--, phosphorus or silicon; and n is an integer from 1 to 4. 
     
     
       2. The composition of claim 1 where said glyoxylamide comprises between about 0.01 to about 30 percent by weight of said composition. 
     
     
       3. The composition of claim 2 wherein R and R 1  are individually selected hydrogen, alkyl of 1 to 4 carbon atoms or phenyl; R 2  is phenyl or substituted phenyl; R 3  is alkylene of 1 to 4 carbon atoms; X is zero or --NH-- and n is 2. 
     
     
       4. The composition of claim 3 wherein said glyoxylamide has the formula ##STR7## 
     
     
       5. The composition of claim 4 wherein said glyoxylamide is phenylglyoxylamide. 
     
     
       6. The composition of claim 4 wherein said glyoxylamide is N,N-diethyl phenylglyoxylamide. 
     
     
       7. The composition of claim 4 wherein said glyoxylamide N-n-butyl phenylglyoxylamide. 
     
     
       8. The composition of claim 4 further comprising a sensitizer or a promoter. 
     
     
       9. The composition of claim 8 wherein said promoter is an organic amine. 
     
     
       10. The composition of claim 3 wherein said glyoxylamide has the formula: ##STR8## 
     
     
       11. The composition of claim 10 wherein said glyoxylamide has the formula ##STR9## 
     
     
       12. The composition of claim 10 wherein said glyoxylamide has the formula ##STR10## 
     
     
       13. The composition of claim 10 wherein said glyoxylamide has the formula ##STR11## 
     
     
       14. The composition of claim 10 further including a sensitizer or a promoter. 
     
     
       15. The composition of claim 14 wherein said promoter is an organic amine. 
     
     
       16. In the method of photopolymerizing an ethylenically unsaturated compound in the presence of a photoinitiator by exposure to actinic radiation, the improvement which comprises employing as said photoinitiator a glyoxylamide of the formula ##STR12## wherein R and R 1  are individually selected hydrogen or hydrocarbon of from 1 to 10 carbon atoms; R 2  is a heterocyclic radical, aryl of from 6 to 14 carbon atoms or mono-, di- or polysubstituted phenyl with substituents selected from the group consisting of alkyl, alkoxy, aryloxy, alkylthio, arylthio and halogen; R 3  is phenyl or --CH 2 ) z   where z is an integer from 2 to 6; X is zero, oxygen, suflur, --NH--, phosphorus or silicon; and n is an integer from 1 to 4.   
     
     
       17. The method of claim 16 wherein said glyoxylamide comprises between about 0.01 to about 30 percent by weight of said composition. 
     
     
       18. The method of claim 17 wherein R and R 1  are individually selected hydrogen, alkyl of 1 to 4 carbon atoms or phenyl; R 2  is phenyl or substituted phenyl; R 3  is alkylene of 1 to 4 carbon atoms; X is zero or --NH-- and n is 2. 
     
     
       19. The method of claim 18 wherein said glyoxylamide has the formula ##STR13## 
     
     
       20. The method of claim 18 wherein said glyoxylamide is phenylglyoxylamide. 
     
     
       21. The method of claim 18 wherein said glyoxylamide is N,N-diethyl phenylglyoxylamide. 
     
     
       22. The method of claim 18 wherein said glyoxylamide is N-n-butyl phenylglyoxylamide. 
     
     
       23. The method of claim 19 further comprising a sensitizer or a promoter. 
     
     
       24. The method of claim 23 wherein said promoter is an organic amine. 
     
     
       25. The method of claim 18 wherein said glyoxylamide has the formula ##STR14## 
     
     
       26. The method of claim 25 wherein said glyoxylamide has the formula ##STR15## 
     
     
       27. The method of claim 25 wherein said glyoxylamide has the formula: ##STR16## 
     
     
       28. The method of claim 25 wherein said glyoxylamide has the formula ##STR17## 
     
     
       29. The method of claim 25 further including a promoter. 
     
     
       30. The method of claim 29 wherein said promoter is an organic amine.